Hydrazine → HCID 178456320, compound

HRID 1090255Notes

Reaction equation

HRID 1090255 reaction equation
ClCC#CCCl.C1(=O)NC(=O)C2=CC=CC=C12.[K].[Na].[N:20]1([CH2:25][C:26]#[C:27][CH2:28][N:29]2C(=O)C3=CC=CC=C3C2=O)[CH:24]=[CH:23][N:22]=[CH:21]1.NN.I.CS[C:45]1[C:53]2[CH:54]=[CH:55][CH:56]=[C:51]3[C:52]=2[C:47](=[CH:48][CH:49]=[CH:50]3)[N:46]=1.I>C(O)C>[N:20]1([CH2:25][C:26]#[C:27][CH2:28][NH:29][C:45]2[C:53]3[CH:54]=[CH:55][CH:56]=[C:51]4[C:52]=3[C:47](=[CH:48][CH:49]=[CH:50]4)[N:46]=2)[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

9

Reactant 7

HCID 9321HydrazineHCID 131821,4-Dichloro-2-butyneHCID 24841Hydrogen iodideHCID 5360545SodiumHCID 13588985N-(4-(1H-imidazol-1yl)2-butyn-1-yl)phthalimideHCID 201506502-Methylthiobenz(cd)indole hydriodideHCID 24194345Phthalimide potassium salt

Product 1

HCID 178456320HCID 178456320, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The sequential reaction of 1,4-dichloro-2-butyne with potassium phthalimide and then the sodium salt of imidazole leads to the formation of N-(4-(1H-imidazol-1yl)2-butyn-1-yl)phthalimide, which upon treatment with hydrazine in boiling ethanol leads to 4-(1H-imidazol-lyl)-2-butyn-1-ylamine. Reaction of the latter compound with 2-methylthiobenz(cd)indole hydriodide in ethanol solution, by the conditions of Example 52 leads to the hydriodide of the title compound which is converted to the free base by treatment with alkali hydroxide solution.

Sources & evidence

ORD record
ord-e2d1154b877b45d5baf2b48acffe8064
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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